# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author ; Klaus Merz Lehrstuhl fuer Anorganische Chemie 1 Ruhr-Universitaet Bochum Universitaetsstrasse 150 D-44780 Bochum Deutschland ; _publ_contact_author_phone '049 234 32-24187' _publ_contact_author_fax '049 234 32-14378' _publ_contact_author_email Klaus.Merz@rub.de _publ_requested_coeditor_name ? #=========================================================================== #== # 2. TITLE AND AUTHOR LIST _publ_section_title ; Photoinduced CO release and cytotoxicity of a tris(pyrazolyl)methane manganese tricarbonyl complex ; loop_ _publ_author_name _publ_author_address 'Johanna Niesel' ; Fakult\"at f\"ur Chemie Ruhr-Universit\"at Bochum Universit\"atsstra\&se 150 44780 Bochum Germany ; 'Antonio Pinto' ; Fakult\"at f\"ur Chemie Ruhr-Universit\"at Bochum Universit\"atsstra\&se 150 44780 Bochum Germany ; "Harmel W. Peindy N'Dongo" ; Fakult\"at f\"ur Chemie Ruhr-Universit\"at Bochum Universit\"atsstra\&se 150 44780 Bochum Germany ; 'Ingo Ott' ; Fakult\"at f\"ur Chemie Ruhr-Universit\"at Bochum Universit\"atsstra\&se 150 44780 Bochum Germany ; 'Ronald Guss' ; Fakult\"at f\"ur Chemie Ruhr-Universit\"at Bochum Universit\"atsstra\&se 150 44780 Bochum Germany ; 'Klaus Merz' ; Fakult\"at f\"ur Chemie Ruhr-Universit\"at Bochum Universit\"atsstra\&se 150 44780 Bochum Germany ; 'Ulrich Schatzschneider' ; Fakult\"at f\"ur Chemie Ruhr-Universit\"at Bochum Universit\"atsstra\&se 150 44780 Bochum Germany ; data_071205t _database_code_depnum_ccdc_archive 'CCDC 670201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 F6 Mn N6 O3 P' _chemical_formula_weight 498.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.669(5) _cell_length_b 11.855(3) _cell_length_c 12.869(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.006(5) _cell_angle_gamma 90.00 _cell_volume 3592.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 0.915 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7708 _exptl_absorpt_correction_T_max 0.9140 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs CCD 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9772 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.27 _reflns_number_total 3203 _reflns_number_gt 2251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+3.1073P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0083(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3203 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.17593(2) 0.09090(6) 0.72119(5) 0.0360(3) Uani 1 1 d . . . N1 N 0.12541(13) 0.2005(3) 0.7496(3) 0.0361(8) Uani 1 1 d . . . O1 O 0.15600(15) -0.0768(3) 0.8654(3) 0.0594(9) Uani 1 1 d . . . C1 C 0.16324(18) -0.0150(4) 0.8069(4) 0.0431(11) Uani 1 1 d . . . P1 P 0.08371(5) 0.35835(11) 0.14409(10) 0.0467(4) Uani 1 1 d . . . F1 F 0.12212(16) 0.4374(3) 0.2474(3) 0.0910(12) Uani 1 1 d . . . C2 C 0.2176(2) -0.0036(5) 0.6829(4) 0.0515(12) Uani 1 1 d . . . O2 O 0.24295(18) -0.0624(3) 0.6558(4) 0.0748(12) Uani 1 1 d . . . N2 N 0.08628(13) 0.2620(3) 0.6590(3) 0.0342(8) Uani 1 1 d . . . F2 F 0.13555(14) 0.3029(4) 0.1406(5) 0.135(2) Uani 1 1 d . . . H1 H 0.0560(16) 0.308(3) 0.488(3) 0.027(10) Uiso 1 1 d . . . O3 O 0.27603(14) 0.1588(3) 0.9385(3) 0.0705(11) Uani 1 1 d . . . N3 N 0.18366(14) 0.2199(3) 0.6242(3) 0.0370(8) Uani 1 1 d . . . C3 C 0.23808(18) 0.1347(4) 0.8542(4) 0.0460(11) Uani 1 1 d . . . F3 F 0.02886(15) 0.4080(3) 0.1439(4) 0.0864(11) Uani 1 1 d . . . N4 N 0.13697(14) 0.2800(3) 0.5518(3) 0.0377(8) Uani 1 1 d . . . C4 C 0.12046(18) 0.2343(4) 0.8420(4) 0.0410(10) Uani 1 1 d . . . H4A H 0.1422 0.2056 0.9184 0.049 Uiso 1 1 calc R . . F4 F 0.04321(11) 0.2780(2) 0.0378(2) 0.0595(8) Uani 1 1 d . . . C5 C 0.07977(19) 0.3163(4) 0.8132(4) 0.0497(12) Uani 1 1 d . . . H5A H 0.0687 0.3530 0.8639 0.060 Uiso 1 1 calc R . . N5 N 0.10447(14) 0.0529(3) 0.5707(3) 0.0365(8) Uani 1 1 d . . . F5 F 0.07935(15) 0.4514(3) 0.0546(3) 0.0779(10) Uani 1 1 d . . . N6 N 0.06938(14) 0.1366(3) 0.5045(3) 0.0370(8) Uani 1 1 d . . . C6 C 0.05886(18) 0.3330(4) 0.6955(4) 0.0411(10) Uani 1 1 d . . . H6A H 0.0305 0.3847 0.6486 0.049 Uiso 1 1 calc R . . F6 F 0.08488(19) 0.2640(3) 0.2318(3) 0.1177(17) Uani 1 1 d . . . C7 C 0.22548(19) 0.2666(4) 0.6121(4) 0.0444(11) Uani 1 1 d . . . H7A H 0.2635 0.2428 0.6521 0.053 Uiso 1 1 calc R . . C8 C 0.2062(2) 0.3551(4) 0.5329(4) 0.0479(12) Uani 1 1 d . . . H8A H 0.2277 0.4013 0.5095 0.057 Uiso 1 1 calc R . . C9 C 0.1498(2) 0.3612(4) 0.4963(4) 0.0417(11) Uani 1 1 d . . . H9A H 0.1242 0.4130 0.4419 0.050 Uiso 1 1 calc R . . C10 C 0.08152(18) -0.0402(4) 0.5126(4) 0.0413(10) Uani 1 1 d . . . H10A H 0.0964 -0.1129 0.5377 0.050 Uiso 1 1 calc R . . C11 C 0.03264(19) -0.0174(4) 0.4096(4) 0.0499(12) Uani 1 1 d . . . H11A H 0.0089 -0.0698 0.3530 0.060 Uiso 1 1 calc R . . C12 C 0.02582(17) 0.0960(4) 0.4068(4) 0.0422(11) Uani 1 1 d . . . H12A H -0.0037 0.1380 0.3478 0.051 Uiso 1 1 calc R . . C13 C 0.08330(17) 0.2509(4) 0.5449(3) 0.0359(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0328(4) 0.0400(4) 0.0283(4) 0.0012(3) 0.0085(3) 0.0013(3) N1 0.0349(19) 0.041(2) 0.0276(18) 0.0015(16) 0.0103(15) -0.0036(15) O1 0.070(2) 0.055(2) 0.050(2) 0.0116(18) 0.0242(18) -0.0066(18) C1 0.040(2) 0.046(3) 0.034(2) -0.002(2) 0.010(2) 0.002(2) P1 0.0452(7) 0.0423(7) 0.0378(7) -0.0002(5) 0.0073(5) -0.0008(5) F1 0.109(3) 0.070(2) 0.0514(19) -0.0116(16) 0.0027(18) -0.035(2) C2 0.050(3) 0.058(3) 0.039(3) 0.005(2) 0.015(2) 0.006(2) O2 0.083(3) 0.074(3) 0.077(3) 0.002(2) 0.046(2) 0.026(2) N2 0.0326(17) 0.038(2) 0.0306(18) -0.0016(15) 0.0139(15) 0.0014(15) F2 0.045(2) 0.100(3) 0.229(6) -0.049(3) 0.038(3) 0.0063(19) O3 0.048(2) 0.090(3) 0.046(2) -0.013(2) -0.0011(17) -0.0127(19) N3 0.0352(19) 0.040(2) 0.0322(19) 0.0000(16) 0.0125(15) -0.0009(16) C3 0.038(2) 0.052(3) 0.040(3) 0.001(2) 0.013(2) 0.002(2) F3 0.097(2) 0.069(2) 0.125(3) -0.020(2) 0.078(2) -0.0068(18) N4 0.0362(19) 0.041(2) 0.0335(19) 0.0014(16) 0.0142(16) -0.0019(16) C4 0.046(2) 0.050(3) 0.029(2) -0.003(2) 0.0185(19) -0.008(2) F4 0.0502(16) 0.0593(18) 0.0514(17) -0.0127(14) 0.0093(13) -0.0051(13) C5 0.048(3) 0.060(3) 0.044(3) -0.015(2) 0.024(2) -0.005(2) N5 0.0356(18) 0.040(2) 0.0281(18) 0.0016(16) 0.0105(15) 0.0008(16) F5 0.107(3) 0.073(2) 0.0548(19) 0.0045(16) 0.0391(18) -0.0290(19) N6 0.0345(18) 0.044(2) 0.0267(18) -0.0010(16) 0.0096(15) -0.0018(16) C6 0.037(2) 0.038(3) 0.046(3) -0.007(2) 0.018(2) -0.0008(19) F6 0.161(4) 0.067(2) 0.057(2) 0.0244(18) -0.005(2) -0.035(2) C7 0.038(2) 0.052(3) 0.043(3) -0.010(2) 0.018(2) -0.007(2) C8 0.059(3) 0.045(3) 0.049(3) -0.007(2) 0.033(2) -0.011(2) C9 0.057(3) 0.037(2) 0.038(2) 0.000(2) 0.028(2) -0.005(2) C10 0.046(2) 0.043(3) 0.037(2) -0.007(2) 0.021(2) -0.008(2) C11 0.051(3) 0.062(3) 0.034(3) -0.018(2) 0.017(2) -0.018(2) C12 0.036(2) 0.063(3) 0.024(2) -0.005(2) 0.0108(18) -0.003(2) C13 0.034(2) 0.040(2) 0.030(2) 0.003(2) 0.0115(18) 0.0018(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 C2 1.803(6) . ? Mn1 C1 1.804(5) . ? Mn1 C3 1.812(5) . ? Mn1 N1 2.025(4) . ? Mn1 N5 2.029(3) . ? Mn1 N3 2.045(3) . ? N1 C4 1.319(5) . ? N1 N2 1.355(4) . ? O1 C1 1.131(5) . ? P1 F2 1.551(4) . ? P1 F1 1.554(3) . ? P1 F5 1.559(3) . ? P1 F3 1.575(3) . ? P1 F6 1.579(4) . ? P1 F4 1.599(3) . ? C2 O2 1.133(6) . ? N2 C6 1.337(5) . ? N2 C13 1.438(5) . ? O3 C3 1.119(5) . ? N3 C7 1.318(5) . ? N3 N4 1.356(5) . ? N4 C9 1.333(5) . ? N4 C13 1.435(5) . ? C4 C5 1.372(7) . ? C4 H4A 0.9400 . ? C5 C6 1.361(6) . ? C5 H5A 0.9400 . ? N5 C10 1.313(5) . ? N5 N6 1.355(5) . ? N6 C12 1.338(5) . ? N6 C13 1.437(5) . ? C6 H6A 0.9400 . ? C7 C8 1.382(7) . ? C7 H7A 0.9400 . ? C8 C9 1.351(6) . ? C8 H8A 0.9400 . ? C9 H9A 0.9400 . ? C10 C11 1.381(6) . ? C10 H10A 0.9400 . ? C11 C12 1.355(7) . ? C11 H11A 0.9400 . ? C12 H12A 0.9400 . ? C13 H1 1.01(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Mn1 C1 92.9(2) . . ? C2 Mn1 C3 91.6(2) . . ? C1 Mn1 C3 88.5(2) . . ? C2 Mn1 N1 175.13(17) . . ? C1 Mn1 N1 90.28(17) . . ? C3 Mn1 N1 92.11(18) . . ? C2 Mn1 N5 91.40(18) . . ? C1 Mn1 N5 93.85(17) . . ? C3 Mn1 N5 176.09(18) . . ? N1 Mn1 N5 84.74(14) . . ? C2 Mn1 N3 92.62(19) . . ? C1 Mn1 N3 174.20(17) . . ? C3 Mn1 N3 93.01(18) . . ? N1 Mn1 N3 84.06(14) . . ? N5 Mn1 N3 84.38(14) . . ? C4 N1 N2 104.5(3) . . ? C4 N1 Mn1 135.6(3) . . ? N2 N1 Mn1 119.9(3) . . ? O1 C1 Mn1 176.1(4) . . ? F2 P1 F1 92.4(2) . . ? F2 P1 F5 92.1(3) . . ? F1 P1 F5 89.78(19) . . ? F2 P1 F3 176.5(2) . . ? F1 P1 F3 90.8(2) . . ? F5 P1 F3 89.3(2) . . ? F2 P1 F6 90.1(3) . . ? F1 P1 F6 91.83(19) . . ? F5 P1 F6 177.2(2) . . ? F3 P1 F6 88.4(2) . . ? F2 P1 F4 88.6(2) . . ? F1 P1 F4 179.0(2) . . ? F5 P1 F4 90.17(17) . . ? F3 P1 F4 88.13(18) . . ? F6 P1 F4 88.17(18) . . ? O2 C2 Mn1 178.2(5) . . ? C6 N2 N1 111.3(3) . . ? C6 N2 C13 129.7(4) . . ? N1 N2 C13 118.7(3) . . ? C7 N3 N4 104.6(3) . . ? C7 N3 Mn1 136.0(3) . . ? N4 N3 Mn1 119.3(2) . . ? O3 C3 Mn1 177.5(5) . . ? C9 N4 N3 111.3(3) . . ? C9 N4 C13 129.7(4) . . ? N3 N4 C13 118.9(3) . . ? N1 C4 C5 111.9(4) . . ? N1 C4 H4A 124.1 . . ? C5 C4 H4A 124.1 . . ? C6 C5 C4 105.2(4) . . ? C6 C5 H5A 127.4 . . ? C4 C5 H5A 127.4 . . ? C10 N5 N6 104.9(3) . . ? C10 N5 Mn1 135.1(3) . . ? N6 N5 Mn1 120.0(3) . . ? C12 N6 N5 111.5(4) . . ? C12 N6 C13 129.9(4) . . ? N5 N6 C13 118.5(3) . . ? N2 C6 C5 107.1(4) . . ? N2 C6 H6A 126.5 . . ? C5 C6 H6A 126.5 . . ? N3 C7 C8 111.3(4) . . ? N3 C7 H7A 124.4 . . ? C8 C7 H7A 124.4 . . ? C9 C8 C7 105.4(4) . . ? C9 C8 H8A 127.3 . . ? C7 C8 H8A 127.3 . . ? N4 C9 C8 107.3(4) . . ? N4 C9 H9A 126.3 . . ? C8 C9 H9A 126.3 . . ? N5 C10 C11 111.0(4) . . ? N5 C10 H10A 124.5 . . ? C11 C10 H10A 124.5 . . ? C12 C11 C10 106.0(4) . . ? C12 C11 H11A 127.0 . . ? C10 C11 H11A 127.0 . . ? N6 C12 C11 106.5(4) . . ? N6 C12 H12A 126.7 . . ? C11 C12 H12A 126.7 . . ? N4 C13 N6 109.3(3) . . ? N4 C13 N2 109.9(3) . . ? N6 C13 N2 109.7(3) . . ? N4 C13 H1 104(2) . . ? N6 C13 H1 113(2) . . ? N2 C13 H1 111(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.660 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.138